


What Could Have Been

by madelinewrites



Category: Supernatural
Genre: Canon Typical Violence, F/M, Sam expressing himself, alluding to hooking up, semi-angst
Language: English
Status: Completed
Published: 2017-07-06
Updated: 2017-07-06
Packaged: 2018-11-28 17:19:37
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,480
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11422575
Author URL: https://archiveofourown.org/users/madelinewrites/pseuds/madelinewrites
Summary: While sitting alone at a bar, Sam feels the need to talk about himself, something he rarely does. Luckily, Jamie is there, and is more than happy to have Sam all to herself.





	What Could Have Been

**Author's Note:**

> Characters: Sam, Dean (mentioned), Jamie (OC bartender)  
> Prompt: Boy In Need by Louden Swain for @mrswhozeewhatsis Louden Swain Mini Bang 2017  
> Summary: While sitting alone at a bar, Sam feels the need to talk about himself, something he rarely does. Luckily, Jamie is there, and is more than happy to have Sam all to herself.  
> Word Count: 2472  
> Warnings: semi-angst, Sam expressing himself, canon typical violence, alluding to hooking up
> 
> A/N: This is kind of a test run to see how OCs do note-wise. If you enjoy this, please give a like or let me know! As always, FEEDBACK IS NEEDED AND LOVED! EVEN A LIKE HELPS!

**“He can’t afford to leave… /He’s a boy in need /He remembers he was twelve years old… /And the path it seemed so clear ahead of him /Now it’s just a race he cannot win. /Just to think he will be 60 years old /Life not wasted, but nothing to show /And he’ll sit down at a table just for him /And think about it, all that could have been.”**

**_Boy In Need – Louden Swain_ **

           Sam tapped at his glass aimlessly, shocked at the gentle  _tink_  that came with every beat. While he didn’t run for monthly manicure’s like Dean had joked earlier, he never let himself become ungroomed. Technically, long nails might be good for their business, the whole hurting and killing monsters thing and all, though he doubted a scratch would do much to a demon.

           He and Dean had stopped at the dive bar to take a load off after hours of continual driving. Dean would never admit it, but he was exhausted. It seemed lately like one hunt right after another, with no real goal or victory. Just a dead monster and another case to hurry to. Sam knew it, no matter how well Dean hid it. They spent so much time together, Sam could read Dean better than he could read himself sometimes.

           They were  _supposed_  to drink together; you know, the wholesome brother bonding time, though that never really works out with Dean. He had persistently hounded the only woman in the place until she finally decided going back to his hotel was a good idea. Sam just rolled his eyes, told his brother to have a goodnight, and caught the keys to the Impala as Dean tossed them. Dean seemed edgy leaving Baby with Sam, but he must’ve needed the relief of a one night stand more than even Sam knew. 

           Every hunter had their vice; Sam was just glad he took on the healthier option of books and coffee. As the thought crossed his mind, Sam nearly laughed at himself. What kind of vice was that? One of some old, rich guy with a wife and a couple of grown kids, or at least that’s what Sam imagined. He was probably the furthest thing from being that guy, though he felt more disappointment than pride in the fact.

           “Hey,” the bartender tapped at the smooth, auburn surface of the bar in front of him. “Want another?”  Sam stared at the bottle, then at the keys in his hand. With a sigh, he placed the keys down, nodding at the woman brusquely.

           “Yeah, that’d be great,” he relented, his voice low. He felt off. He wished Dean had stayed, which was strange for Sam. Not that he didn’t enjoy having his brother around, but he was never one to pass up some alone time. He didn’t know how long he’d sit there without Dean telling him it was time to go; sometimes, Sam just really fell into the place of the little brother. He murmured a thank you to the bartender, attempting a small smile. She looked at him strangely, grabbing a washcloth and wiping the bar down near him.

           “You seem a bit down,” she commented, peeking at Sam from her peripheral. He shrugged, flashing a tired smile.

           “Long day,” he explained, thankful for her kindness but also wildly uncomfortable. Dealing with questions from those outside the hunting sphere was just an exhausting acting job, though something in him right then hardly cared. He just wanted to talk.

           “Yeah,” she muttered, her eyes widening. “I’ve been here since ten.” Sam nodded, understanding as always,

           “Bet you’re tired,” he remarked.

           “Understatement,” she laughed, tossing the washcloth aside and resting her arms on the bar, face to face with him. “I feel like I’ve been here forever.”

           “How long have you been bartending?” Sam asked, thankful for a distraction from his thoughts.

           “God,” she sighed, rubbing her eyes as she thought. “It’s gotta be over twenty years now. Depressing when you put it like that.”

           “You don’t like bartending?” Sam asked sincerely, his brows furrowing.

           “I don’t know,” she sighed. “It’s all I know I guess. I know I couldn’t work no cubicle job, yet… I don’t know. Sometimes I just kinda wonder if there was more out there for me if I’d have just looked. Now, I’m too old to move on. Pretty much stuck, you know?”

           “Oh yeah,” Sam muttered, sipping his drink. “I know.” She raised an eyebrow.

           “You bartend?” Sam laughed, shaking his head.

           “No, no, I don’t know much about alcohol besides the drink in my hand. Just…I just get feeling stuck.” She tilted her head inquisitively, looking him up and down.

           “You don’t look like you’d be stuck,” she observed. Sam squinted his eyes.

           “What do you mean?” She shrugged, and as she spoke, Sam heard an ever-subtle southern accent come out. There was something strikingly endearing about it.

           “I don’t know, you just seem like you’d have it all together. You’re obviously intelligent; I’d guess college educated. You’re handsome, you’re strong, you speak well. I don’t know how you’re not succeeding. What do you do?”

           “Well, first off, thank you,” Sam said. “I did go to college for a little while, Stanford actually, but, uh, had to drop out.”

           “Stanford?” she whistled. “Called that one. So, why’d you drop out?” He looked away; here came the improv.

           “Well…at first it was just a little family emergency but then…I don’t know. I just realized I couldn’t keep running; I was going to be in the… _family business_  whether I walked willingly into it or was dragged. I chose the first, after finally coming to terms with my role in all of it,” Sam expressed, the words simultaneously pouring from his mouth while also being meticulously thought out. Everything had to be carefully phrased; the last thing he wanted was to somehow drag  _her_  into the whole mess that was his life.

She nodded, mulling over his words for a moment. Sam took the opportunity to take her in; long chocolate brown hair tied loosely in a ponytail, revealing her petite ears. Her nose was a little crooked, but it fit her somehow. Her bottom lip was full and her top lip only a little less so. Her skin was clear, excluding the sprinkling of freckles over her nose and cheeks. She looked cute, though Sam couldn’t pinpoint her age. She looked like she could be just a little over twenty, though she said she’d been working for over twenty years. The age difference didn’t deter him though; there was something about her that felt…different.

“Do you not like this ‘family business’ you’re in?” she finally asked, her voice quiet.

“Yes and no,” Sam admitted. “I mean, I love my brother and our friend Cas but…I guess I just wanted more out of life than the job.”

“What do you want, Sam?” she asked simply. It wasn’t that complicated of a question, yet Sam had trouble answering it.

“I don’t know,” he confessed, putting out his hands. “If you would have asked me years ago, I would have told you I wanted a normal life. Nice job at some law firm, a wife that I loved, some kids, nice house, maybe a dog or two, the whole thing. And I still see that as fulfilling, I really do, just like I did back in college, but now… It’s more than just feeling too old to achieve it. I feel like I’d be an imposter, playing a part that’s not meant for me.”

“Does it make you sad? Knowing you’re never going to get it?” she pressed.

“No,” Sam answered, thinking. “Not  _sad_ , just…existential, if that makes sense. I’m only 34, I know I probably have quite a few years yet, but I thought the same thing at 22 when I got back into this job. Over ten years have passed, and I’m still doing this. I have my brother, I have Cas, and at the end of the day, we’ve done a lot of good. I know that. But what’s the point of it all? I haven’t achieved any of  _my_  goals. Soon, another ten years will be gone, then another, and on it goes till I’m done, my story ends. And what will I have to show for all of it besides plenty of enemies and few friends?”

           Again, she thought for a while, but this time, Sam could hardly stand the silence. He had completely unloaded all his baggage onto this stranger, an extremely underpaid bartender that probably just wanted some easy conversation. Treating her like a therapist somehow felt manipulative.

           “I’m sorry,” Sam muttered, running a hand through his hair and laughing awkwardly. “I didn’t mean to put so much on you. What bartender wants to play therapist?”

           “Oh, trust me, you’re not close to the worst ‘patient’ I’ve had.” She rolled her eyes. “Anyway, it’s been nice hearing you talk since I, uh, I’ve been feeling the same way. I never used to want all that but I just keep getting older and nothing ever becomes…fulfilling.”

           “I haven’t even asked your name, yet I’m telling you all my inner thoughts,” Sam chuckled. She widened her eyes, a smile coming across her lips.

           “Wow, that’s weird. Feels like we’ve known each other for a while, doesn’t it? I’m Jamie.” She extended out a hand, her expression quickly becoming flirty. Usually, Sam would entirely brush it off; what’s the point of getting close to someone when all you bring to them is danger? But there was something in him that just needed it, needed to feel wanted. He didn’t plan on making it a habit, but he was in need of a simple one night stand.

           “Sam,” he replied, taking her hand in his and shaking gently. She nodded, repeating the name as she looked him up and down.

           “That fits you,” she approved. “Well,  _Sam_ , how would you feel about us leaving this place…together?”          

           “Don’t you have to work?” Sam asked.

           “Look around you,” she laughed. “The place is empty, it’s time to close.” He followed her orders and was shocked to see that she was right. He must’ve been there for over an hour, just talking about himself to someone he’d just met.

           “Wow,” he chuckled, throwing a fifty on the bar. “I guess, I should probably pay out then.”

           “Sam, your tab is only like ten bucks,” she informed, printing out his receipt.

           “I know,” he assured. “The rest is for you. A little extra for the added therapy.” She laughed, cashing him out and counting all her tips from the night. She stuffed whatever money she earned into her jeans, beginning to turn off some lights.

           “So, uh,” she began tentatively. “Is that a no, to the whole us leaving together thing?” Sam smiled, shaking his head.

           “Should we take your car or mine?” he murmured, standing up. She seemed shocked at his height, now having to look up to him.

           “Yours,” she replied, breathless.

           She finally was done with closing up, shutting off all the lights as they finally walked out of the bar together. She locked the door and walked side by side with Sam, sneaking glances up at him as they made their way towards Baby.

           “Where’s your car?” Sam asked, looking around at the entirely abandoned parking lot.

           “Oh, uh, I parked in the back,” she assured quickly. Sam just nodded, a little confused. Dean had driven in through the back when they got there, and there were no cars to be seen behind the building.

           They finally reached the Impala, and Sam stopped for a moment, looking down at Jamie. Her eyes were sparkly in the moonlight, the warm brown seeming like shiny silk in the dim light. She was lovely, and Sam definitely felt desire for her, but he had to be sure.

           “I feel like I need to loosen up some more,” Sam explained, pulling out one of Dean’s old flasks. He took a giant gulp, feigning a grimace.

           “Strong stuff?” she inquired, laughing.

           “Yeah,” Sam chuckled, wiping his mouth and handing the flask to her. “Have some.” She willingly complied, taking a large gulp. Sam knew that his suspicions were true when she began screaming. He grabbed the flask for her hand as she clawed at her throat.

           “Damn Winchesters,” she snarled, her eyes turning black. “You always make everything harder.”

           She jumped at him quickly, practically drooling at the thought of being the one to kill a Winchester, making Sam lose his grip on the flask of holy water. As she was about to wrap her hands around his throat, he reached his arm out and swatted, scratching her face. She growled at the sting, giving Sam just enough time to roll her over and bang her head against the side of the Impala. Assured that she was entirely knocked out, Sam pushed her off and stood up, breathing heavy. She looked so innocent, even when passed out with scratches on her face, though he supposed that was exactly what the demon had wanted when possessing her. No one would ever look at a girl like Jamie, if that really was her name, and imagine her hurting someone. It was the perfect meat suit for somebody ready to do plenty of harm. He looked around to make sure there were no cameras, before starting the exorcism chant. After seeing the black flow out of her, he gently picked her up and placed her in the back seat of his car.

She had no ID or even a phone, no way for Sam to find where she actually belonged. He decided to book her own room at the hotel just so she could wake up somewhere safe and with people to help her if necessary. Being possessed wasn’t a great feeling, Sam would know. He gently laid her on the bed, taking a few more bills out of his wallet and setting it on the nightstand beside her.

“You deserve it, Jamie,” he muttered, looking back into the room one more time before leaving, finally returning to his own room.

           He sighed as he collapsed on the bed, the night entirely not working out as planned. Even with all the chaos, he did feel better. He kept all his problems so stuffed inside of his head, just swirling around and becoming larger than they actually were. Talking actually helped, and after getting over the initial discomfort of the vulnerability, it wasn’t that stressful to open up. He doubted he was in the perfect mental state after just one “session”, but it was at least a start. And while his trust had been entirely misplaced, Sam at least learned one thing.

           The nails were  _definitely_ good for business.

**Author's Note:**

> Also found at: http://deansleather.tumblr.com/post/162645611342/what-could-have-been


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